N-bromobutanimide → Methyl 2-(5-bromothiophen-2-yl)acetate

HRID 523135

반응식

HRID 523135 반응식
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][C:7]([O:9][CH3:10])=[O:8].C1C(=O)N([Br:18])C(=O)C1>CN(C=O)C.CCOCC>[Br:18][C:5]1[S:1][C:2]([CH2:6][C:7]([O:9][CH3:10])=[O:8])=[CH:3][CH:4]=1

참가 물질

5

반응물 2

HCID 67184N-bromobutanimideHCID 88055Methyl thiophen-2-acetate

생성물 1

HCID 12403315Methyl 2-(5-bromothiophen-2-yl)acetate수율 82.1%

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

Referring once again to FIG. 3, a solution of methyl 2-(thiophen-2-yl)acetate (27.44 g, 175.7 mmol) was dissolved in DMF (500 mL) and stirred in the dark as NBS (37.52 g, 210.8 mmol) was added portion wise. The reaction was stirred for three hours at which TLC indicated completion of the reaction. The reaction was diluted with ether and the organic phase was washed with ammonium chloride and water, then dried with magnesium sulfate and concentrated by rotovap. The resulting crude oil was purified by triturating with hexanes, decanting off the organic phase above the oil, then subjecting the oil to chromatography on a gradient plug of silica gel (hexanes to 10% EtOAc in hexanes) to yield the product as a yellow oil (33.90 g, 144.2 mmol, 82%). The product matches literature data. Kranich, R., et al., “Rational Design of Novel, Potent Small Molecule Pan-Selectin Antagonists,”J. Med. Chem. 50:1101-1115 (2007). 1H NMR (CDCl3) δ: 6.89 (d, J=4.0 Hz, 1H), 6.69 (dt, J=4.0 Hz, 1H), 3.76 (s, 2H), 3.72 (s, 3H).

후처리

  1. additionwas added portion wise
  2. customcompletion of the reaction
  3. washthe organic phase was washed with ammonium chloride and water
  4. dry with materialdried with magnesium sulfate
  5. concentrationconcentrated by rotovap
  6. customThe resulting crude oil was purified
  7. customby triturating with hexanes
  8. customdecanting off the organic phase above the oil

출처 및 근거

ORD 기록
ord-5efbc0656c2c4d6e9752578cd6a68f87
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334304B2

연결된 노트

불러오는 중…